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WO1997039891A1 - Stratifies decoratifs fabriques sous pression elevee avec des resines de melamine thermodurcissantes modifiees par sorbitol - Google Patents

Stratifies decoratifs fabriques sous pression elevee avec des resines de melamine thermodurcissantes modifiees par sorbitol Download PDF

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Publication number
WO1997039891A1
WO1997039891A1 PCT/US1997/006820 US9706820W WO9739891A1 WO 1997039891 A1 WO1997039891 A1 WO 1997039891A1 US 9706820 W US9706820 W US 9706820W WO 9739891 A1 WO9739891 A1 WO 9739891A1
Authority
WO
WIPO (PCT)
Prior art keywords
sorbitol
resin
laminate
melamine
formaldehyde
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US1997/006820
Other languages
English (en)
Inventor
Ben Gapud
Mark A. Peters
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
GP Chemicals Equity LLC
Original Assignee
Georgia Pacific Resins Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Georgia Pacific Resins Inc filed Critical Georgia Pacific Resins Inc
Priority to AU27410/97A priority Critical patent/AU2741097A/en
Publication of WO1997039891A1 publication Critical patent/WO1997039891A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08G12/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with substituted triazines
    • C08G12/32—Melamines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/04—Layered products comprising a layer of synthetic resin as impregnant, bonding, or embedding substance
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B44—DECORATIVE ARTS
    • B44C—PRODUCING DECORATIVE EFFECTS; MOSAICS; TARSIA WORK; PAPERHANGING
    • B44C5/00—Processes for producing special ornamental bodies
    • B44C5/04—Ornamental plaques, e.g. decorative panels, decorative veneers
    • B44C5/0469—Ornamental plaques, e.g. decorative panels, decorative veneers comprising a decorative sheet and a core formed by one or more resin impregnated sheets of paper
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
    • C08G12/40—Chemically modified polycondensates
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones
    • D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
    • D21H17/51—Triazines, e.g. melamine
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H27/00—Special paper not otherwise provided for, e.g. made by multi-step processes
    • D21H27/18—Paper- or board-based structures for surface covering
    • D21H27/22—Structures being applied on the surface by special manufacturing processes, e.g. in presses
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31859—Next to an aldehyde or ketone condensation product
    • Y10T428/31862—Melamine-aldehyde
    • Y10T428/31866—Impregnated or coated cellulosic material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31942—Of aldehyde or ketone condensation product
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31942—Of aldehyde or ketone condensation product
    • Y10T428/31949—Next to cellulosic

Definitions

  • the present invention relates to decorative high-pressure laminates made with sorbitol-modified, melamine-formaldehyde resins, and to methods of making the high- pressure laminate.
  • the high-pressure laminates can be used for furniture, countertops or flooring.
  • Aminoplast resins are often used in the saturation of decorative and overlay paper for the preparation of decorative laminates because of their excellent color, hardness, and solvent, water, and chemical resistance. They are also resistant to heat and abrasion. Many patents exist describing the use of aminoplast resins in these applications. Unfortunately, unmodified melamine resins have very short shelf lives, e.g., 1-3 days, after which time the resin begins to separate from solution. Laminates produced from such unmodified aminoplast resins also are very brittle and cannot be post-formed to produce clear, crack- free surfaces. Many of the shortcomings of unmodified aminoplast resins can be addressed by the introduction of various resin modifiers.
  • These modifiers can increase the shelf life of aminoplast resins, can increase flow during processing, can increase the cured resin's flexibility, and/or can be used to increase post-formability of a laminated product.
  • a plasticizer is added to aminoplast formulations to improve shelf life and to aid post- formability.
  • Suitable plasticizers which have been used in this regard include sucrose, sorbitol, alkylguanamines, aliphatic polyols, aromatic amides, aromatic amines, polyvinyl alcohol, monocarbamates, caprolactam, isocyanuarates, etc.
  • 3,716,395 describes a laminated material which contains, inter alia, a coating layer comprised of, for example, melamine- and/or urea-formaldehyde resins, a pigment, and a plasticizer.
  • a coating layer comprised of, for example, melamine- and/or urea-formaldehyde resins, a pigment, and a plasticizer.
  • the steps taken to improve post-formability often create laminates whose color, clarity, or chemical and water resistance are adversely affected.
  • sugar-modified melamine-formaldehyde resins often yellow when subjected to heat and pressure as the laminate is cured. This is particularly a problem for products made by a high-pressure lamination.
  • the object of the present invention is to modify a thermosetting melamine-formaldehyde (MF) resin with sorbitol such that the color of the final, high- pressure laminate using the resin is much improved, as compared to conventional MF resins which use sucrose as a plasticizer, while still producing a post-formable laminate which maintains its chemical and water resistance.
  • the present invention is directed to a high- pressure laminate comprising a substrate impregnated with a sorbitol-modified melamine- formaldehyde resin and subjected to a pressure of about 1000 to 2000 psi during cure.
  • the sorbitol modified melamine formaldehyde resin comprises the reaction product of an aqueous, alkaline solution of formaldehyde, melamine, and sorbitol.
  • 3,194,719 are prepared from the co-condensation products of an aminotriazine, an aldehyde, and either an anhydride of sorbitol, an oiefin oxide of sorbitol, or a 1,3,4,6-sorbide, respectively.
  • sorbitol itself is an effective modifier for a resin used in a high-pressure lamination process.
  • Figure 1 depicts the color comparison (b*) of laminate samples as a function of cure temperature.
  • Figure 2 depicts the color comparison (L*) of laminate samples as a function of cure temperature.
  • the present invention relates to a process of making a decorative, high-pressure laminate using a thermosetting, sorbitol-modified melamine resin.
  • High-pressure laminates produced with a sorbitol-modified melamine resin are clearer (more transparent) and less yellow than laminates made with sugar- (sucrose) modified resins.
  • "high-pressure” is defined as a pressure of generally between about 1000 and 2000 psi.
  • an aqueous solution of formaldehyde is combined with melamine and sorbitol and reacted under alkaline conditions. Water is added before, during, or after the reaction is complete so that the resin contains about 40-60% solids. The temperature of the reaction mixture is held between about 60 °C and atmospheric reflux until a final water tolerance of 200-400% by volume is reached. The resin at this water tolerance is stable for about 4-6 weeks at 25 °C.
  • melamine is specifically mentioned in the practice of this invention, the melamine may be totally or partially replaced with other suitable amine-containing compounds.
  • Suitable compounds include urea, thiourea, dicyandiamide, melem, melam, melon, ammeline, ammelide, substituted meiamines, guanamines, or mixtures thereof.
  • Substituted meiamines include the alkyl meiamines and aryl meiamines which can be mono-, di-, or tri-substituted. In the alkyl-substituted meiamines, each alkyl group can contain 1 to 6 carbons and, preferably, 1 to 4 carbons.
  • Typical examples of some of the alkyl-substituted meiamines are monomethylmelamine, dimethyl melamine, trimethyl melamine, monoethyl melamine, and l-methyl-3-propyl-5 -butyl melamine.
  • each aryl group can contain 1-2 phenyl moieties and, preferably, 1 phenyl moiety.
  • Typical examples of an aryl-substituted melamine are monophenyl melamine or diphenyl melamine. Based on considerations of cost and availability, standard melamine is generally preferred.
  • the guanamines which can be employed in the practice of this invention can be of any of the cycloaliphatic guanamines.
  • the cycloaliphatic guanamines should not contain more than 15 carbon atoms.
  • Typical examples of some of the cycloaliphatic guanamines are tetrahydrobenzoguanamine, hexahydrobenzoguanamine, 3-methyl- tetrahydrobenzoguanamine, 3-methyl-hexahydrobenzoguanamine, 3,4-dimethyl-l,2,5,6- tetrahydrobenzoguanamine, and 3,4-dimethylhexahydrobenzoguanamine and mixtures thereof.
  • a preferred cycloaliphatic guanamine is tetrahydrobenzoguanamine.
  • Mixtures of aminotnazine compounds include melamine and an alkyl substituted melamine, such as tetrahydrobenzoguanamine, or melamine and a cycloaliphatic guanamine, such as tetrahydrobenzoguanamine.
  • Other guanamines which might be used include acetoguanamine, formoguanamine, or benzoguanamine.
  • Formaldehyde can be used alone or in combination with a variety of other aldehydes or their equivalents heretofore employed in the formation of melamine resins including, for example, acetaldehyde, propionaldehyde, butylaldehyde, furfuraldehyde, benzaldehyde, acrolein, methacrolein, and crotonaldehyde.
  • the aldehydes employed have the general formula R'CHO, wherein R' is a hydrogen or hydrocarbon moiety generally containing 1 to 8 carbon atoms.
  • Formaldehyde is preferred in most applications.
  • Formaldehyde can be supplied in any one of its commonly available forms, including formalin solutions and paraformaldehyde.
  • Formaldehyde is generally used as an aqueous solution at a concentration of 30-50%.
  • the formaldehyde-to-melamine mole ratio is preferably between about 1.2 and 2.0 and, more preferably, between about 1.5 to 1.8 in the reaction mixture.
  • Sorbitol is added to the aqueous formaldehyde solution prior to, concurrently with, or after the addition of the melamine, the sorbitol is added at a concentration of 1 to 30%, preferably at a concentration of 1 to 12%, based on the total weight of the ultimately formed resin.
  • the alkaline conditions of the reaction mixture of the present invention may be achieved simply by adding a base to the reaction mixture to achieve a pH of between 7 and 11, preferably between 8.5 and 10.5 and, more preferably, between about 9.0 and 9.5.
  • Suitable bases include, but are not limited to, alkali metal hydroxides, such as sodium, lithium, or potassium hydroxide.
  • Other bases include alkali metal carbonates, such as sodium carbonate and potassium carbonate, alkaline earth hydroxides, such as magnesium hydroxide, calcium hydroxide and barium hydroxide, aqueous ammonia, and amines, such as triethanolamine.
  • Additives typically used in melamine-formaldehyde resins also may be added to the previously prepared resin of the invention, for example fire retardants, pigments, extenders, fillers, catalysts, and the like. It is well known to those skilled in the art to add appropriate additives, as required, to improve particular laminate properties.
  • catalysts include inorganic acids, e.g., sulfuric, hydrochloric, phosphoric, boric, etc.; organic acids and anhydrides, e.g., acetic, tartaric, benzoic, propionic, adipic, oxalic, fumaric acids, hexachloric phthalic anhydride, maleic anhydride, etc.
  • organic acids and anhydrides e.g., acetic, tartaric, benzoic, propionic, adipic, oxalic, fumaric acids, hexachloric phthalic anhydride, maleic anhydride, etc.
  • Other catalysts which can be employed are those which liberate acid when heated.
  • Such catalysts include the amine salts of organic and inorganic acids, such as the hydrochloric salt of 2-amino-2-methyl propanol, the hydrochloric salt of mono-, di-, or triethanol amine, the hydrochloric salt of 2-dimethylamino-2-methyl propanol, the amine salts of para-toluene sulfonic acid, the chloroacetic acid salt of pyridine, the triammonium acid pyrophosphate salt of aminomethyl propanol, the phosphoric acid salt of 2-dimethylamino-2-methyl propanol, ethylene sulfite, etc.
  • Other catalysts include the inorganic salts of inorganic acids, such as ammonium chloride, magnesium chloride, zinc chloride, etc.
  • the catalyst system might also include mixtures of the aforementioned catalysts.
  • Catalysts are added in an amount from about 0.1 to 10 wt%, preferably about 0.1 to 1.5 wt% and, most preferably, about 0.2 wt%, based on the resin solids.
  • the catalyst may be added in the reaction vessel or to the laminating syrup immediately prior to preparation of a laminate.
  • Laminates can be prepared from (1) a rigid substrate, (2) a melamine resin impregnated decorative sheet, and, in some cases (3) a melamine resin impregnated overlay sheet.
  • the rigid substrate may consist of any suitable material, such as particle board, a resin-binded wood fiberboard, a plurality of phenolic resin-impregnated sheets, etc. These composites are heated under high pressure to form a single component which can be incorporated into furniture, used on countertops or flooring, etc.
  • the amount of resin inco ⁇ orated into these laminates varies from 30% to 80% based on the weight of the total laminate, and depends on the type of application and the type of materials used to make the laminate. The lower percentages are generally used for decorative print sheets and the higher in overlay sheets.
  • the laminate is then formed in this fashion under a specific pressure (generally 1000-2000 psi) and temperature (generally 250-350°F) for periods of 5 to 45 minutes.
  • the laminate made in this manner must then pass several physical tests, including post-formability and resistance to boiling water.
  • the hydrophobe is the point at which the water becomes cloudy.
  • the reaction mixture was then cooled to 85 °C and held there until the condensation reaction reached a water tolerance of 200-400% by volume.
  • Water tolerance is determined by adding water dropwise to 10 ml of resin adjusted to 25 °C, until the resin turns turbid. The volume of water used is divided by the volume of resin and multiplied by 100 to obtain the % water tolerance of the resin. This is a relative measure of the degree of molecular weight advancement of the resin; a lower water tolerance reflects a more advanced resin.
  • White decorative paper was saturated with sorbitol-modified melamine resin catalyzed with an amine blocked toluene sulfonic acid and B-staged at 150°C for 1 min. After B-staging, 2 impregnated sheets of paper were sandwiched around another unimpregnated sheet and cured under 1000 psi of pressure at 127°C for 5 mins. Other laminates were made in a similar fashion but were cured at 138, 150, 163, and 177°C under pressure for 5 mins.
  • Laminates were made in an analogous fashion to that described in example 2 with the exception that the sugar modified-melamine/formaldehyde resin was used to impregnate the decorative paper.
  • L*, a*, and b* is a three-dimensional measurement of color tone.
  • the L* value measures the lightness (whiteness, higher L* value) or darkness (blackness, lower L* value) of a color.
  • the a* value measures the redness (higher +a* value) or greenness (lower -a* value) of a color.
  • the b* value measures the yellowness (higher +b* value) or blueness

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Laminated Bodies (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Abstract

Stratifié décoratif fabriqué sous pression élevée avec une résine de mélamine-formaldéhyde modifiée par sorbitol et son procédé de fabrication.
PCT/US1997/006820 1996-04-23 1997-04-22 Stratifies decoratifs fabriques sous pression elevee avec des resines de melamine thermodurcissantes modifiees par sorbitol Ceased WO1997039891A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU27410/97A AU2741097A (en) 1996-04-23 1997-04-22 Decorative, high-pressure laminates made with thermosetting melamine resins modified with sorbitol

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/636,607 1996-04-23
US08/636,607 US5820997A (en) 1996-04-23 1996-04-23 Decorative high-pressure laminates made with thermosetting melamine resins modified with sorbitol

Publications (1)

Publication Number Publication Date
WO1997039891A1 true WO1997039891A1 (fr) 1997-10-30

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PCT/US1997/006820 Ceased WO1997039891A1 (fr) 1996-04-23 1997-04-22 Stratifies decoratifs fabriques sous pression elevee avec des resines de melamine thermodurcissantes modifiees par sorbitol

Country Status (3)

Country Link
US (1) US5820997A (fr)
AU (1) AU2741097A (fr)
WO (1) WO1997039891A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2085217A1 (fr) * 2008-01-17 2009-08-05 Cesaplast S.p.A. Procédé de production de stratifié fin à formé pour revêtir des surfaces décoratives et stratifié obtenu associé

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Publication number Priority date Publication date Assignee Title
US20050287383A1 (en) * 2004-06-29 2005-12-29 Taylor John G Fire and smoke resistant panels and laminates for vehicles and method of manufacture
GB201004538D0 (en) * 2010-03-18 2010-05-05 Dynea Oy Resin composition for the manufacture high gloss laminated panels
DE102015103514B4 (de) * 2015-03-10 2019-05-09 Fritz Egger Gmbh & Co. Og Verfahren zur Herstellung eines Laminates, Laminat erhältlich nach dem Verfahren, Verwendung eines Härters für Aminoplastharze zur Herstellung solcher Laminate
CN114960294A (zh) * 2022-06-01 2022-08-30 上海贝辉木业有限公司 一种耐龟裂的浸渍纸及其制备方法

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US3194722A (en) * 1963-05-07 1965-07-13 Monsanto Co Melamine laminating resin modified with an olefin oxide of sorbitol

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2085217A1 (fr) * 2008-01-17 2009-08-05 Cesaplast S.p.A. Procédé de production de stratifié fin à formé pour revêtir des surfaces décoratives et stratifié obtenu associé

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Publication number Publication date
US5820997A (en) 1998-10-13
AU2741097A (en) 1997-11-12

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